How To Start a Conversation With a Stranger Via Chat

If you’ve ever felt awkward trying to start a conversation with someone you didn’t know, then you need to know for free that you’re not alone. We’ve all had similar experiences at one point of our lives, whether at our workplace, a meeting, or an occasion. Kick-starting a conversation with a total stranger can be very daunting, but with the right social skills, one can easily achieve it like a walk in the park.

Truth be told, learning to initiate striking conversations with individuals, especially strangers will help foster new relationships–whether work-related or casual–, and most importantly build one’s confidence. In this article, you’ll discover practical ways you can converse with strangers.

But here are some tips you need to put in check before we go any further:

  • Study the individual before starting any conversation. If he/she seems busy, try to keep the conversation short.
  • Remain positive all through the conversation.
  • Mind your body language.
  • Take deep breaths before starting any conversation to ease off nervousness.

20 Different Ways to Start Conversation With a Stranger

These are ways you can initiate meaningful conversations in the future. Depending on the scenario or situation, you can try any of these approaches outlined below;

Ask for Information

This is one effective way of kick starting a conversation with a stranger. By asking questions, depending on the situation can help foster captivating conversations. You can ask about the weather, traffic, or what they intend doing next.

For example: If you’re stuck in traffic, you can start by asking, “Please, does this always happen? How long do you think the traffic will last?”

Another thing to note is to be a good listener so you can think of comments to keep the conversation open.

Pay a Compliment

Everyone loves to feel good and be complimented from time to time. It’s a natural feeling that brings a sort of fulfillment and self-worth. So, starting up a conversation with a complement is a good way to go.

For example: You can start by complimenting someone’s shoes, “I like your shoes, they look so nice.”

You might want to follow up by asking where they got it from, or the brand of the item.

Ask About Current Happenings

This would require you to be knowledgeable about current events. It can be a good conversation starter. Nevertheless, it’s advisable to stay away from topics that can trigger arguments and offence, topics on politics, religion, etc. You can always talk about the news, sports, carnivals, concerts, or even a new movie.

For example: Ask, “The carnival will definitely start next week, and it will be held in the town square.” Will you be attending?”

Introduce Yourself

This is simple and straightforward and is quite effective, especially if there’s no other way to start up the conversation. A typical scenario is when you just moved into a new  apartment or environment and you want to get familiar with your new neighbors.

For example, “Good Morning my name is Christabel”, I am the new occupant of flat 4″

You’re most likely to receive a welcoming response with such an introduction.

Talk About a Shared Topic

There are instances where you can use your surroundings to initiate conversation with a stranger. It could be at an event, where you could ask the individual how he/she is enjoying the event. Another instance could be at an office reception, you can ask the person sitting beside you, what he/she came for.

Example: “Are you also here for the interview? I’m feeling really nervous”.

Open-ended Questions Come in Handy

Asking open-ended Questions can foster longer conversation time with a stranger. This works best when you and the stranger are present at the same event. You can easily ask about what they think about the event.

For example: “Frankly speaking, the groom danced more than the bride.” What do you think?”

With this, if the individual is willing to respond, he/she could even talk about past events and experiences, thereby making the chat more interesting.

Seek Their Opinion

This strategy works best if you’re out somewhere like the library, or out for lunch, or even at a supermarket. Things like these can be asked: “This is the math book I usually use, but I think I should try using a different one.” What do you believe?”

Lend a Helping Hand

This is a great way to start a chat with a total stranger. You can offer to help someone if you see them struggling with something. It could be a new neighbor struggling to get their luggage out of the car trunk.

Example: “Can I help you carry your box? You must be new in town.”

Of course, everybody needs help at one point or the other, unless the stranger insists–which is most likely not to happen.

Think About an Interesting Fact to Talk About

This strategy only works best when your “interesting fact” directly relates with your location or the situation on ground. For example when traveling by air, attending an art exhibition, or when working on farmland. For instance: “Africa is the world’s second-biggest continent.” Know what I mean?”

Keep it Short

Being direct or straightforward is also an excellent way to converse with an individual. It applies when asking for directions, when trying to ask for help, or when you want to try out something new for the first time. For example: “I’m sorry to bother you, but I can’t find my way to the mess hall. Hope you wouldn’t mind me joining you?”

Ask for Their Advice

You can ask a stranger for advice to start up a conversation with him/her. It could be someone you met at a conference, or your classmate, or a professional in your field. Let’s look at this example:

Example: “Hi! Please, can you help me check out my list of topics for our seminar next week. I’m not sure which one to pick, I could use your advice.”

Viral Video Approach

Hopefully this could foster other related conversations. It is better to talk about a video that the content is appropriate and won’t be tagged offensive. Because not everyone can stomach certain things.

An example is this: “Have you seen the latest  dancing video challenge trending on TikTok  ?”

Background Check

Asking for a Stranger’s background is a great way to begin a conversation. It’s professional and also welcoming. It could be welcoming an individual joining a new group, or a new team at work. Check out this example:

Example: “ Guess what, the beautiful lady with me here is Miss Nkechi, she is a part of the company henceforth. Where are you from?”

Make Intelligent Comments

This is not limited to face-to-face conversations, it also applies to the online space–on social media pages. Making intelligent comments on a topic or an observation can make strangers comfortable around you. For example:

Commenting on an observation: “I see you prefer sitting by the window during classes rather than sitting in the middle.”

At some point, we’ve checked out an individual’s profile on social media just because they commented brilliantly.

Common Interest Approach

You can use this approach when you sense you share a common interest with the stranger. For instance, the stranger could be wearing your club’s jersey, or carrying an item that’s similar to the one you have at home.

You can start by saying this: “I see you’re a Chelsea fan, I’m also a fan. Did you watch the last game? It was really great!”

Ask for Their Help

You can kick start a discussion by asking for someone’s help. It’s an effective way to initiate a chat and it works well in most cases. You can ask for help at a gym, or at an event. Consider this example:

You can ask the gym Instructor for help: “I haven’t used this exercising tool before, and I’m not really Sure how it works, can you please help me out?”

Talk About a Shared Trait

Imagine sharing a unique trait with someone sitting beside you, it would be so relaxing to talk about it with each other. Once you’re sure that you share a common trait with the stranger, you can form an instant connection with him/her.

For example: “I noticed you can raise your brow one at a time – same here too! Isn’t it so cool?”

Comment on a Shared Activity

Another way to kick start a conversation with a stranger is to comment on a shared activity or interest. For instance, you might see a stranger holding a souvenir from an event you attended, or a person eating your favorite snack. Check out this example:

Example: “Cyril, this souvenir looks so much like the one that was shared during the inaugural lecture . I have one like that too, did you attend the lecture as well?”

A Good Joke Will do the Magic

If you’re good at telling jokes, then it’s one way to get a stranger talking to you. Of course, you wouldn’t want to tell a joke that’s not relevant to the situation, it would only make you look like the joke itself. 

Comment Professionally

This approach is more relatable when you want to approach someone you’ve been admiring or you would like to work with. It could be a keynote speaker at an event, or a business man or woman you would like to learn a few things from. See this example:

Example: “Hello ma’am, I was overwhelmed with your performance at the conference. Would it be possible to book an appointment with you this week?”

Why You Need to Talk With Strangers

When you were a child, you must have been advised severally never to talk with strangers–that was great advice and still is for children. But now you’re older and still shy away from speaking with strangers. 

Remember the saying that “No man is an Island” or the business saying that “Your money is with strangers”, it really comes into play in our day to day lives.

Whether you know it or not, we communicate for a living and cannot do without meeting new people from time to time. So, here are few reasons why it’s necessary to converse with strangers:

  • There’s something new to learn: the truth is, you cannot know it all and it will surprise you to know that a simple conversation with a stranger can add to your knowledge bank.
  • Opportunities and Influence: meeting new people and fostering meaningful conversations can become a life saver for your personal growth, profession or business.
  • You become better: believe it or not, talking to people is a skill, and as with most other skills, the more you keep learning and practicing, the better you become.

Avoid These Phrases

So, now, you know that talking to strangers is not a bad idea, but you have to be extra careful about what you say. The last thing you want is to get into an argument with an individual you just met or a group of strangers.

As much as possible, try to avoid sensitive or awkward topics such as these:

  • Religion and religious affairs 
  • Politics
  • Race and racism
  • Sexual issues
  • Gender based violence
  • Gossips
  • Money matters
  • Divorce and marriage matters


No matter where you find yourself, you’ll always come in contact with strangers–it’s inevitable. It’s true that starting a conversation with someone you don’t know is never easy, but it’s a social skill that can be worked on and mastered with time.

Earlier, you read that opportunities can spring from casual conversations with strangers, and it is often said that communication is the key to influence. Now, imagine the number of opportunities you might have missed, just because you did not initiate “that” conversation.

Don’t get it all mixed up though, you’re not being asked to talk with every stranger you encounter, that would be totally unrealistic. As a matter of fact, not everyone would be willing to speak to you, and you shouldn’t let that get to you as well.

The bottom line is this: talking to individuals, especially strangers can be very rewarding, and give you a sense of belonging. Your challenge is to break the ice and continue with a couple of well placed questions. Also, having a couple of starter sentences can help make it worthwhile.

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